Most managers have a mental list of conversations they have been meaning to have for weeks. Not new ones — the ones that started as something simple and became difficult through postponement. A feedback conversation about quality that waited until it became a conduct issue. A tension between two team members that waited until the relationship had broken down entirely. The avoidance is usually the decision that costs the most, and it is almost never recognised as a decision at all.
This is a practical guide for working managers on how to prepare for and run difficult conversations — the kind involving performance, behaviour, a pattern that needs changing, or a disagreement that has calcified into silence.
What makes a conversation difficult
Not the content, usually. The manager who tells someone their promotion application was unsuccessful, delivered honestly and with care, does not have a difficult conversation. The manager who has been avoiding telling someone their work is not good enough for four months, and now has to say it in a formal setting, has one.
Most conversations become difficult through delay. The subject has time to calcify. Stakes accumulate. The other person fills the silence with their own interpretation, which is rarely more favourable than the truth. The gap between what needs to be said and what has been said widens until crossing it requires real effort.
There are conversations that are hard by their nature — redundancy, serious misconduct, situations where someone’s personal circumstances are affecting their work. But for most working managers, the majority of difficult conversations are difficult because they were not had earlier, simply and directly, when they would have been considerably easier.
Preparation is most of the work
The conversation itself rarely fails in the moment. It fails before it starts.
Three things need to be clear before you sit down.
What specifically is the problem? Not “the attitude” or “not being a team player” — the observable behaviours and outputs. “In the last three client presentations, the figures were wrong. In two of them, the client flagged this before we did.” Specifics give the other person something to engage with. Generalities give them something to deflect, or to carry home and worry about without being able to act on.
What outcome do you want? A change in specific behaviour, documented and agreed? A better understanding of what is blocking this person? An honest conversation about whether the role is still the right fit? Knowing what success looks like changes how you structure the meeting. “I want them to feel better about it” is not an outcome. “I want to leave with a shared understanding of what changes are needed and a date to review progress” is.
What is their likely view of the situation? This is the step most managers skip. You have a version of events. They have one too. The more different they are, the harder the conversation — and the more useful it is to have thought about their perspective before you sit down. You will not always be right. But going in with a working hypothesis about what they are thinking, and staying genuinely curious about whether it is accurate, makes you significantly more effective.
A short written note to yourself before any difficult conversation — what happened, what outcome you want, what their perspective might be — takes ten minutes and halves the chance of the conversation going sideways.
A framework worth knowing
The researchers Stone, Patton and Heen, in their work at the Harvard Negotiation Project, make a useful observation: most difficult conversations are actually three conversations running simultaneously, and managers tend to handle only one of them.
The “what happened” conversation is the surface layer — who did what, who said what, whose version of events is correct. This is where most managers spend all their time, and where most conversations get stuck. Two people can look at the same set of facts and draw opposite conclusions; neither is simply lying.
The feelings conversation runs underneath — what each person is experiencing emotionally, and what the conversation threatens for them. A manager raising a performance concern may feel anxious about the relationship. The employee may feel ambushed, embarrassed, or — not uncommon — quietly relieved that someone is finally saying it out loud. Neither is mentioning any of this, but both are shaped by it.
The identity conversation runs deepest — what this interaction means about the kind of person I am. “If I’m being criticised for this, does that mean I’m incompetent? Disliked? Not actually trusted here?” People do apparently irrational things in difficult conversations because they are, at some level, defending their own self-narrative.
You do not need to be a therapist to use this model. What it gives you is permission to notice when someone has shifted from debating facts to defending their sense of themselves — and to respond to that rather than press harder on the facts.
Running the conversation
Open with the specific situation, not the verdict
“Your work hasn’t been good enough” is a verdict. “Three of the last five client briefs contained errors the client raised before we did” is a situation. Start with the situation. The verdict can follow — naming it clearly is important — but opening with observable specifics anchors the conversation in something shared rather than something contested.
The SBI model from the Centre for Creative Leadership is a useful structure here: Situation (when and where it happened), Behaviour (what specifically occurred), Impact (what it caused). “In last Thursday’s handover meeting, when you interrupted the project lead twice to correct their figures in front of the client, the client noticed — and the project lead came to me afterwards to say they felt undermined.” That is a set of facts both parties can examine. “You need to be less aggressive in meetings” is not.
Ask before you prescribe
After stating the situation and its impact, ask: “What’s your read on what happened?” Most managers underestimate how much this changes the conversation. You might learn something that genuinely alters the picture — the employee was working from faulty data, or is dealing with something outside work, or has a concern about a colleague they have not felt safe raising. You might not. Either way, asking and visibly listening before moving to what needs to change does two things: it respects the possibility that your version is incomplete, and it makes the other person feel heard enough to engage with what comes next.
Be direct about what needs to change
The most common failure in difficult management conversations is excessive softening. The feedback sandwich — say something positive, say the difficult part, close with something positive — has been taught so widely and used so badly that most people now hear the bread and ignore the filling. They leave feeling vaguely reassured and nothing changes.
The difficult message needs to be delivered clearly. Not harshly — the way you say something matters — but clearly enough that the person would not be surprised to see it summarised in a follow-up email. “This needs to change” is a complete sentence. “I just wanted to flag that there might be some room for development here, if you felt that was something you wanted to explore” is not a message; it is a hint in a suit.
Agree what happens next, and write it down
The conversation should end with a shared understanding of what changes, by when, and how you will both know whether it has. A brief note or email within 24 hours — not a formal document, simply a summary of what was discussed and agreed — is one of the most useful habits a working manager can develop. It protects both parties, reduces the “I didn’t realise that’s what you meant” problem three weeks later, and signals that the conversation was serious.
When it goes badly
Even well-prepared conversations derail. Some common patterns, and what to do:
The person becomes very distressed. Pause. Acknowledge it directly: “This is clearly hard to hear — do you want a few minutes?” Pressing on through visible distress is rarely effective and sometimes makes things significantly worse. The conversation can continue; it does not need to continue right now.
The person denies everything. You are probably in a version dispute. Resist the impulse to press harder on your account. Instead: “It sounds like you experienced this quite differently. Help me understand how you saw it.” Sometimes this unlocks useful information. Sometimes it does not. Either way, you have been fair, and the documentation of what was said protects you both.
The person deflects by raising a grievance about you. Not the most common, but not rare: the employee responds to a concern by surfacing one of their own — “You’re only saying this because you’ve never liked me.” The instinct is to defend yourself immediately. The better response is to separate the two threads: “I’d like to keep this conversation focused on [the specific issue]. If you have concerns about how I’ve managed you, I take that seriously — and I’d like to have a separate conversation about it.” Then return to the original issue.
The person goes completely silent. Do not fill the silence with more content. Acknowledge the difficulty. Give it a moment. People sometimes shut down because they are absorbing something significant, or deciding whether to trust you. Patient silence is more useful than anxious monologue.
After the conversation
A common mistake is treating the conversation as finished once you leave the room. The days immediately afterwards matter more than most managers expect.
Follow up within 24 hours with a brief written summary of what was discussed and agreed. Check in briefly within the week — not as surveillance, but as evidence that the conversation was not a one-off event to be forgotten. Look for early signs of change and name them, without turning the observation into excessive praise for what is essentially expected behaviour.
And if things do not change: have the next conversation earlier than feels comfortable, not later than is defensible. The managers who are genuinely effective in this area are the ones who do not allow the gap between conversations to grow wide enough that the next one becomes a different kind of difficult.
Related reading
- Communication skills — active listening, body language, and the foundations that make difficult conversations possible
- Performance management — the wider framework of expectations, appraisals, and review cycles in which most difficult conversations sit
- Conflict, negotiation and influencing — for situations where the conversation has gone past feedback into dispute
Managers who want to build confidence in feedback, conflict, and performance conversations can find structured CPD pathways at SkillsCircle, developed by Accipio. For those looking to formalise their management development with a recognised qualification, Aicura offers CMI-accredited leadership programmes, including levy-funded apprenticeship routes.